5,6-trans-1a,25-Dihydroxyvitamin D3 - CAS 73837-24-8
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
5,6-trans-1a,25-Dihydroxyvitamin D3
Catalog Number:
73837-24-8
Synonyms:
Calcitriol Impurities A;1,3-Cyclohexanediol,4-methylene-5-[(2E)-2-[(1R,3aS,7aS)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-,(1R,3S,5E)-;5,6-trans-Calcitriol;(1R,3S,5E)-4-Methylene-5-[(2E)-2-[(1R,3aS,7aS)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol;(1α,3β,5E,7E)- 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol;1,25-Dihydroxy-5,6- trans-vitamin D3;1α,25-Dihydroxy-5,6-trans-vitamin D3;5-{2-[1-(5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexane-1,3-diol;(1R,3S,E)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-Methylenecyclohexane-1,3-diol;(6R)-6-[(1R,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(diMethyl)silyl]oxy]-2-Methylene-cyclohexylidene]ethylidene]-7a-Methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-Methyl-heptan-2-ol
CAS Number:
73837-24-8
Description:
5,6-trans-1a,25-Dihydroxyvitamin D3 is an impurity of Calcitriol, which is the hormonally active form of vitamin D and is the active metabolite of vitamin D3. It is the trans isomer of Calcitriol.It is used as a control product to study calcitriol.
Molecular Weight:
416.64
Molecular Formula:
C27H44O3
Quantity:
Grams to Kilograms
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
InChI:
InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10?,21-11+/t18-,22-,23-,24+,25+,27+/m1/s1
InChIKey:
GMRQFYUYWCNGIN-QEKNMNSZSA-N
Chemical Structure
CAS 73837-24-8 5,6-trans-1a,25-Dihydroxyvitamin D3

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Reference Reading


1.Low serum vitamin D levels are associated with shorter survival after first-line azacitidine treatment in patients with myelodysplastic syndrome and secondary oligoblastic acute myeloid leukemia.
Radujkovic A1, Schnitzler P2, Ho AD3, Dreger P3, Luft T3. Clin Nutr. 2016 Feb 10. pii: S0261-5614(16)00048-0. doi: 10.1016/j.clnu.2016.01.021. [Epub ahead of print]
BACKGROUND & AIMS: Azacitidine (AZA) therapy has become the recommended first-line treatment for patients with high-risk myelodysplastic syndromes (MDS) and oligoblastic (<30% bone marrow blasts) acute myeloid leukemia (AML). However, improvement of the efficacy of AZA treatment remains a challenge. We retrospectively tested the hypothesis that VitD levels (25-hydroxyvitamin D3) prior to start of first-line AZA therapy are predictive of overall survival (OS) in patients diagnosed with MDS and secondary oligoblastic AML. Furthermore, the antiproliferative effects of AZA in combination with 25-hydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3 were investigated in vitro.
2.A rapid method for the separation of vitamin D and its metabolites by ultra-high performance supercritical fluid chromatography-mass spectrometry.
Jumaah F1, Larsson S2, Essén S1, Cunico LP1, Holm C2, Turner C1, Sandahl M3. J Chromatogr A. 2016 Apr 1;1440:191-200. doi: 10.1016/j.chroma.2016.02.043. Epub 2016 Feb 17.
In this study, a new supercritical fluid chromatography-mass spectrometry (SFC-MS) method has been developed for the separation of nine vitamin D metabolites within less than eight minutes. This is the first study of analysis of vitamin D and its metabolites carried out by SFC-MS. Six columns of orthogonal selectivity were examined, and the best separation was obtained by using a 1-aminoanthracene (1-AA) column. The number and the position of hydroxyl groups in the structure of the studied compounds as well as the number of unsaturated bonds determine the physiochemical properties and, thus the separation of vitamin D metabolites that is achieved on this column. All D2 and the D3 forms were baseline separated with resolution values>1.5. The effects of pressure, temperature, flow rate and different gradient modes were studied. Electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) were compared in positive mode, both by direct infusion and after SFC separation.
3.Generation and characterization of two immortalized human osteoblastic cell lines useful for epigenetic studies.
Pérez-Campo FM1,2, May T3, Zauers J3, Sañudo C1, Delgado-Calle J1,4,5, Arozamena J1, Berciano MT6, Lafarga M6, Riancho JA7. J Bone Miner Metab. 2016 Apr 2. [Epub ahead of print]
Different model systems using osteoblastic cell lines have been developed to help understand the process of bone formation. Here, we report the establishment of two human osteoblastic cell lines obtained from primary cultures upon transduction of immortalizing genes. The resulting cell lines had no major differences to their parental lines in their gene expression profiles. Similar to primary osteoblastic cells, osteocalcin transcription increased following 1,25-dihydroxyvitamin D3 treatment and the immortalized cells formed a mineralized matrix, as detected by Alizarin Red staining. Moreover, these human cell lines responded by upregulating ALPL gene expression after treatment with the demethylating agent 5-aza-2'-deoxycytidine (AzadC), as shown before for primary osteoblasts. We further demonstrate that these cell lines can differentiate in vivo, using a hydroxyapatite/tricalcium phosphate composite as a scaffold, to produce bone matrix.
4.The vitamin D receptor (VDR) gene rs11568820 variant is associated with type 2 diabetes and impaired insulin secretion in Italian adult subjects, and associates with increased cardio-metabolic risk in children.
Sentinelli F1, Bertoccini L1, Barchetta I2, Capoccia D1, Incani M3, Pani MG3, Loche S4, Angelico F2, Arca M2, Morini S5, Manconi E3, Lenzi A1, Cossu E3, Leonetti F1, Baroni MG6, Cavallo MG2. Nutr Metab Cardiovasc Dis. 2016 Feb 19. pii: S0939-4753(15)30260-X. doi: 10.1016/j.numecd.2016.02.004. [Epub ahead of print]
BACKGROUND AND AIMS: 1α,25-dihydroxyvitamin-D3, the biologically active vitamin D, plays a central role in several metabolic pathways through the binding to the vitamin D receptor (VDR). VDR has been shown to be involved in cardiovascular diseases, cancer, autoimmunity and type 2 diabetes mellitus (T2DM). Several polymorphisms in the VDR gene have been described. Among these, the rs11568820 G-to-A nucleotide substitution was found to be functional, modulating the transcription of the VDR gene. Objective of this study was to perform an association study between rs11568820 polymorphism and T2DM in a cohort of Italian adults with T2DM and in non-diabetic controls. To add further insight into the role of VDR gene we explored whether this association begins early in life in overweight/obese children, or becomes manifest only in adulthood.